Piperazine → Tert-butyl-dimethyl-piperazin-1-ylsilane

HRID 590532Notes

Reaction equation

HRID 590532 reaction equation
[NH:1]1[CH2:6][CH2:5][NH:4][CH2:3][CH2:2]1.C1(C)C(C)=CC=CC=1.[C:15]([Si:19]([CH3:22])([CH3:21])Cl)([CH3:18])([CH3:17])[CH3:16].[OH-].[Na+]>C1(C)C=CC=CC=1>[Si:19]([N:1]1[CH2:6][CH2:5][NH:4][CH2:3][CH2:2]1)([C:15]([CH3:18])([CH3:17])[CH3:16])([CH3:22])[CH3:21]

Participants

6

Reactant 4

HCID 4837PiperazineHCID 7237O-XyleneHCID 14798Sodium HydroxideHCID 28928tert-Butyldimethylsilyl chloride

Product 1

HCID 19434780Tert-butyl-dimethyl-piperazin-1-ylsilane

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
110 °C

Procedure

A flask equipped with a stirrer, reflux condenser; dropping funnel and thermometer was charged with 1076.3 g (12.5 mol) of piperazine and 500 ml of xylene and heated at 110° C. Once the internal temperature became steady, 1507.0 g (5.0 mol) of a 50 wt % toluene solution of t-butyldimethylchlorosilane was added dropwise over 3 hours. Stirring was continued for 2 hours at the temperature. The reaction solution was cooled to room temperature, to which 2,500 g of a 10 wt % sodium hydroxide aqueous solution was added. The organic layer was separated. On distillation, 646.6 g of a fraction having a boiling point of 70-71° C./0.2 kPa was collected, which was 1-t-butyldimethylsilylpiperazine.

Workup

  1. customA flask equipped with a stirrer
  2. temperaturereflux condenser
  3. additionwas added
  4. customThe organic layer was separated
  5. distillationOn distillation, 646.6 g of a fraction
  6. customwas collected

Sources & evidence

ORD record
ord-e9b2874cf014485aab18a4d0e6e23f22
Source dataset
uspto-grants-2016_01
Patent number
US09233988B2

Reaction notes

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